Work

Haloselective Cross-Coupling via Ni/Photoredox Dual Catalysis

Year: 2017

Type: article

Abstract: The chemoselective functionalization of polyfunctional aryl linchpins is crucial for rapid diversification. Although well-explored for Csp2 and Csp nucleophiles, the chemoselective introduction of Csp3 groups remains notoriously difficult and is virtually undocumented using Ni catalysts. To fill this methodological gap, a “haloselective” cross-coupling process of arenes bearing two halogens, I and Br, using ammonium alkylbis(catecholato)silicates, has been developed. Utilizing Ni/photoredox dual catalysis, Csp3–Csp2 bonds can be forged selectively at the iodine-bearing carbon of bromo(iodo)arenes. The described high-yielding, base-free strategy accommodates various protic functional groups. Selective electrophile activation enables installation of a second Csp3 center and can be done without the need for purification of the intermediate monoalkylated product.

Source: ACS Catalysis

DOI: 10.1021/acscatal.7b01773

Authors: Kingson Lin, Rebecca J. Wiles, Christopher B. Kelly, Geraint H. M. Davies, Gary A. Molander

Institution: University of Pennsylvania

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, University of Pennsylvania, National Institutes of Health, National Institute of General Medical Sciences